The previous Office Action mailed 16 June 2026, is hereby vacated and replaced with the corrected Office Action below.
DETAILED ACTION
The previous Office Action included a typographical error, improperly rejecting claims 20 and 21, which depend from claim 13, where claim 13 depends from claim 1, which has been withdrawn for the reasons discussed below. Furthermore, the previous Office Action omitted the nonstatutory double patenting rejection presented in the Non-Final Office Action mailed 12 May 2025.
This Office Action is correcting the typographical error, and including the nonstatutory double patenting rejection, and is in response to Applicant’s Amendment and Remarks filed on 24 February 2026 in which claims 1 and 10 were amended, and the Remarks filed 11 August 2026.
Claims 1-16, 18 and 20-23 are pending in the current application. Claims 1-10, 13-16, 18 and 20-23 are withdrawn as being drawn to a non-elected invention. Claims 11 and 12 are examined on the merits herein.
Notice of Pre-AIA or AIA Status
The present application, filed on or after March 16, 2013, is being examined under the first inventor to file provisions of the AIA .
Claim Status
Some of the claims submitted 24 February 2026, previously indicated as withdrawn, do not contain the correct status identifier (e.g. withdrawn).
Election/Restrictions
Previously presented claims 2-4, 6-10 and 14-16 remain withdrawn as being drawn to a non-elected invention.
Claims 1, 5, 13, 18 and 20-23 are now withdrawn as being drawn to a non-elected invention, because independent claim 1 has been amended to require a crosslinked product “wherein the alkyl polyglucoside is cross-linked via hydroxypropyl linkages formed by reaction with epichlorohydrin and/or Cl-CH2CH(OH)-CH2-Cl”.
According to the Specification, when an alkyl polyglucoside is reacted with epichlorohydrin, it can react with another alkyl polyglucoside to give a crosslinked product to give
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(see para [0048]-[0050]). This can then be functionalized with
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to give a structure that appears to be the same as the compound recited in withdrawn claim 3, drawn to Group III, which was non-elected.
Thus, the alkyl polyglucoside crosslinked via hydroxypropyl linkages as required by amended claim 1, and functionalized with
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, is the same structure as withdrawn claim 3.
Thus, claim 1 as amended is drawn towards the same subject matter as claim 3, which was withdrawn as being drawn to a non-elected invention.
Accordingly, claims 1, 5, 13, 18 and 20-23 are also withdrawn as being drawn to a non-elected invention.
Applicant’s arguments regarding an additional search or examination burden are not found persuasive, as these are not requirements when making a restriction between multiple inventions in a 35 U.S.C. §371 application.
Withdrawn Rejections
Applicant’s amendment, filed 24 February 2026, with respect to the rejection of claims 1, 5, 11-13, 18 and 20-23 under 35 U.S.C. § 112(b), second paragraph, for indefiniteness, has been fully considered and is persuasive.
The rejection is hereby withdrawn.
Maintained Rejections
Claim Rejections - 35 USC § 103
In the event the determination of the status of the application as subject to AIA 35 U.S.C. 102 and 103 (or as subject to pre-AIA 35 U.S.C. 102 and 103) is incorrect, any correction of the statutory basis (i.e., changing from AIA to pre-AIA ) for the rejection will not be considered a new ground of rejection if the prior art relied upon, and the rationale supporting the rejection, would be the same under either status.
The following is a quotation of 35 U.S.C. 103 which forms the basis for all obviousness rejections set forth in this Office action:
A patent for a claimed invention may not be obtained, notwithstanding that the claimed invention is not identically disclosed as set forth in section 102, if the differences between the claimed invention and the prior art are such that the claimed invention as a whole would have been obvious before the effective filing date of the claimed invention to a person having ordinary skill in the art to which the claimed invention pertains. Patentability shall not be negated by the manner in which the invention was made.
This application currently names joint inventors. In considering patentability of the claims the examiner presumes that the subject matter of the various claims was commonly owned as of the effective filing date of the claimed invention(s) absent any evidence to the contrary. Applicant is advised of the obligation under 37 CFR 1.56 to point out the inventor and effective filing dates of each claim that was not commonly owned as of the effective filing date of the later invention in order for the examiner to consider the applicability of 35 U.S.C. 102(b)(2)(C) for any potential 35 U.S.C. 102(a)(2) prior art against the later invention.
Claim(s) 11 and 12 (all in-part) are rejected under 35 U.S.C. 103 as being unpatentable over Jin et al. (J. Surfact. Deterg., 2016, vol. 19, pp. 885-891, cited in previous Office Action) in view of O’Lenick, Jr. et al. (US Patent No. 7,087,571; hereinafter the ‘571 Patent, cited in previous Office Action) and O’Lenick, Jr. et al. (US Patent No. 8,268,766; hereinafter the ‘766 Patent, cited in previous Office Action).
Jin et al. is concerned with the synthesis of alkyl monoglucoside citric monoester (title). The alkyl groups vary in length where R is a C8, C10 or C12 alkyl, and the reaction is performed in the presence of a strong base:
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(scheme 1; the difference between the structure is pointed out with an arrow, i.e. “-CH2-CH(OH)-CH2-”). Disodium alkyl polyglucosides citrate (APG-EC) prepared from corn starch, citrus juice and natural oil, is a sugar-based green anionic surfactant that is safe and mild (p.885, first para). Furthermore, APG-EC has reduced irritation to eyes and skin. The citrate functionality improves the solubility issues with APG. “Because of its excellent water-solubility, APG-EC aqueous solutions remain clear and bright after prolonged storage near 100 °C.” (p.885, first para). It also has many improved performance attributes, including excellent foaming, and hard water resistance. It can be applied to cosmetics, beauty care products and detergents. Jin et al. teach other alkyl polyglucosides (APG) derivatives have been prepared, including sulfonate and sulfosuccinate APG (p.885, first para).
Jin et al. do not expressly disclose a polymerizing agent as recited in claims 11 and 12, or a structure incorporating the polymerizing agent of claims 11 and 12, i.e. “-CH2-CH(OH)-CH2-”.
The ‘571 Patent teaches a composition having an alkyl polyglucoside of formula (a),
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, where R is an alkyl having 8 to 22 carbon atoms; R1, R2, R3 and R4 are independently selected from the group consisting of -CH2CH(OH)CH2-R12 and H, with the proviso that R1, R2, R3 and R4 are not all H; R12 is
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, a dicarboxylate group, where M is selected from Na, K, and NH4 (claim 1). The above compound is prepared by reacting glyceryl chlorohydrin (Cl-CH2-CH(OH)CH2OH) with maleic anhydride (a dicarboxylate containing moiety). The reaction conditions are mild, and employ sodium methylate (col.11, examples, lines 20-67). The obtained surfactants have “outstanding detergency and foam properties as well as emolliency properties and humectant properties. These surfactants are of particular importance for use in personal care applications like bubble bath, shampoos and body wash. They are also very good additives for hard surface cleaners and detergent systems” (col.11:62-67).
The ’766 Patent teaches preparing alkyl polyglucosides derivatized with sorbitan esters (title). The alkyl polyglucoside is reacted with Cl-CH2CH(OH)CH2-Cl and sorbitan ester:
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(col.3-4). The ‘766 Patent teaches reacting alkyl polyglucoside with the sorbitan ester and a family of epoxy compounds allows for an excellent emulsifier to be obtained under mild aqueous conditions (col.3:57-63). The alkyl polyglucoside (examples 1-9), the sorbitan ester (examples 10-16) are mixed with 1,3-dichloroisopropanol and sodium methylate (examples 27-37). The 1,3-dichloro-isopropanol reacts with the first hydroxyl group to give the following intermediate:
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(col.5: 9-15).
It would have been obvious to one of ordinary skill in the art before the effective filing date of the claimed invention to incorporate an isopropanol linker between the glucoside and citrate of the disodium alkyl polyglucosides citrate taught by Jin et al.
The skilled artisan would have been motivated to react an alkyl glucoside with 1,3-dichloro-isopropanol prior to further functionalizing the alkyl glucoside with citric acid, because the ‘766 Patent teaches the reaction conditions are mild compared to the use of the strong sodium hydroxide base utilized in Jin et al.
The ordinary artisan would have been motivated to use the isopropanol linker -CH2-CH(OH)-CH2- because in the same field of endeavor for preparing surfactants, the ‘571 Patent and ‘766 Patent teach modifying alkyl polyglycosides with the isopropanol linker, which can subsequently be functionalized with a carboxylic acid containing moiety. The ‘571 Patent teaches an alkyl polyglucoside having an isopropanol linker conjugated to a succinate group, a disodium dicarboxylate group. The ‘766 Patent teaches an alkyl polyglucoside having an isopropanol linker conjugated to a sorbitan ester, a carboxylate group. Jin et al. teach an alkyl polyglucoside conjugated to a citrate ester, a trisodium tricarboxylate group.
The ordinary artisan would have been motivated to optimize the alkyl monoglucoside citric monoester of Jin et al., because Jin et al. teach alkyl polyglucoside functionalized with citric acid esters produce no irritation to the eyes, and have excellent storage stability. The compound also possesses other similar desirable properties described by the ‘571 and ‘766 Patents, including foaming, hard water resistance and water-solubility. Like the alkyl polyglucosides of the ‘571 and ‘766 Patents, it can be used in cosmetics, beauty care products and detergents in general.
Claims 11 and 12 are product-by-process claims. The ‘571 Patent teaches reacting the chloro glycerin with the maleic anhydride prior to functionalizing the alkyl polyglucoside. Thus, the product-by-process limitation of claim 11, wherein the isopropanol linker is first reacted with a carboxylate ester, was known before the effective filing date of the claimed invention. Thus, it would have been obvious to react the isopropanol linker with citric acid prior to functionalizing the alkyl polyglucoside.
The use of Cl-CH2-CH(OH)-CH2-Cl as a polymerizing agent was known, and taught by the ‘766 Patent. Thus, it would have been obvious to prepare the alkyl polyglucoside using Cl-CH2-CH(OH)-CH2-Cl, or 1,3-dichloro-isopropanol as recited in claim 12.
Thus, the claimed invention as a whole is prima facie obvious over the combined teaching of the prior art.
Response to Arguments
Applicant’s arguments filed 11 August 2026 with respect to He et al. are not found persuasive.
However, solely to simplify discussion of the present application, the discussion of He et al. is removed.
Applicant argues the treatment of claim 12 is inconsistent with the withdrawal of claim 1.
The above argument is not found persuasive. As discussed above, claim 1 as amended, is now drawn towards the subject matter of claim 3, which is non-elected Group III.
Claim 12, however, is drawn towards preparing the elected species, mono-adduct 1 (structure 1), which is obtained by reacting an alkyl polyglucoside with 3-chloro-2-hydroxypropyl citrate, wherein 3-chloro-2-hydroxypropyl citrate was prepared by reacting epichlorohydrin (with citric acid).
Claim 12 recites “The composition of claim 11, prepared by further reacting with at least one polymerizing agent of the following formula…”. In light of the election of mono-adduct 1, claims 11 and 12 have been interpreted to include the steps of first reacting epichlorohydrin with citric acid to arrive at the first “at least one functionalizing agent” of claim 11:
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(3-chloro-2-hydroxypropyl citrate), (see p.19-20 of the present Specification).
The product obtained by performing the steps in claims 11 and 12 is not the same as what would be obtained by performing the steps in amended claim 1, because claim 1 specifies the obtained product is cross-linked, which in light of Specification is interpreted to mean at least two alkyl polyglucosides are cross-linked together: “wherein the alkyl polyglucoside is cross-linked via hydroxypropyl linkages formed by reaction with epichlorohydrin and/or Cl-CH2-CH(OH)-CH2-Cl. Claims 11 and 12 do not recite cross-linking or obtaining a cross-linked product.
It is also noted, in the 28 July 2025 response to the Restriction Requirement and species election, Applicant specified claims 1-16, 18 and 20-23 reads on mono-adduct 1 (structure 1). Claim 11, an independent claim, and claim 12 were not amended. Thus, they are both properly examined as part of the elected invention and species. Claim 12 has been interpreted as including a step of preparing the 3-chloro-2-hydroxypropyl citrate of claim 11, by reacting epichlorohydrin with citric acid.
Applicant contends Jin provides no teaching that the directly esterified product should be modified by inserting a hydroxypropyl group between the glucoside and citrate. Applicant agues the improved water solubility, storage stability, foaming, hard-water resistance, and reduced irritation are properties of Jin’s directly esterified product. Applicant argues there is no explanation for why a skilled artisan would have altered Jin’s structure to include a hydroxypropyl linkage.
The above argument is not found persuasive, because the citrate moiety is what conferred the improved properties for the alkyl polyglucoside as a surfactant. Furthermore, in the same field of endeavor of preparing alkyl polyglucoside-based surfactants, the secondary references (the ‘571 Patent and ‘766 Patent) teach modifying an alkyl polyglucoside with various carboxylic acid containing functional groups via a hydroxypropyl linkage.
As acknowledged by Applicant, the ‘766 Patent teaches preparing various alkyl polyglucosides having hydroxypropyl linkages and containing additional functional groups like alkoxy, sulfate, sulfonate, quaternary, phosphate, and sorbitan esters. One of ordinary skill in the art would have been motivated to functionalize alkyl polyglucosides with any one of the above described functional groups or citrate, when the ‘766 Patent is considered in combination with Jin et al. and the ‘571 Patent. The prior art as a whole show alkyl polyglucoside surfactants can be modified with a hydroxypropyl linker, and various functional groups to improve the surfactant properties of alkyl polyglucosides. Thus, the ordinary artisan would have known alkyl polyglucosides with improved surfactant properties have been prepared with direct esterification of citric acid or had carboxylic acid moieties introduced via hydroxypropyl linkages. Furthermore, the skilled artisan would have had a reasonable expectation of success in preparing a compound having alkyl polyglucoside with a hydroxypropyl linker bonded to a citrate, and having the same or similar surfactant properties as discussed by Jin et al.
In response to applicant's argument that the references fail to show certain features of the invention, it is noted that the features upon which applicant relies (i.e., claim 12 requires “further reacting the particular composition of claim 11 with that reagent (Cl-CH2CH(OH)-CH2-Cl) as a polymerizing agent) are not recited in the rejected claim(s). Although the claims are interpreted in light of the specification, limitations from the specification are not read into the claims. See In re Van Geuns, 988 F.2d 1181, 26 USPQ2d 1057 (Fed. Cir. 1993).
Claim 12 recites (emphasis added), “The composition of claim 11, prepared by…” is broadly and reasonably interpreted as being drawn towards a step (a precursor step) that results in the composition of claim 11. It is not interpreted as modifying the product obtained in claim 11.
Furthermore, claims 11 and 12 are product-by-process claims, and do not require the prior art to perform the steps recited in claim 11, since patentability is based on the product itself, i.e. “a composition comprising an alkyl polyglucoside functionalized with a citrate ester group”.
Applicant contends there is no evidence the prior art method results in the product of claim 11.
The above argument is not found persuasive. The specification shows reacting an alkyl polyglucoside with 3-chloro-2-hydroxypropyl citrate, as recited in claim 11 results in the elected mono-adduct, i.e. an alkyl polyglucoside-CH2-CH(OH)-CH2-citrate, which structure is obvious for the reasons discussed above (see p.16 of the present Specification). Since the prior art references also teach preparing an alkyl polyglucoside-CH2-CH(OH)-CH2-maleate and alkyl polyglucoside-CH2-CH(OH)-CH2-sorbitan, the ordinary artisan would have had a reasonable expectation of success in arriving at the claimed compound/composition.
For the above stated reasons, said claims are properly rejected under 35 U.S.C. 103(a). Thus, the rejection is hereby maintained.
Double Patenting
The nonstatutory double patenting rejection is based on a judicially created doctrine grounded in public policy (a policy reflected in the statute) so as to prevent the unjustified or improper timewise extension of the “right to exclude” granted by a patent and to prevent possible harassment by multiple assignees. A nonstatutory double patenting rejection is appropriate where the conflicting claims are not identical, but at least one examined application claim is not patentably distinct from the reference claim(s) because the examined application claim is either anticipated by, or would have been obvious over, the reference claim(s). See, e.g., In re Berg, 140 F.3d 1428, 46 USPQ2d 1226 (Fed. Cir. 1998); In re Goodman, 11 F.3d 1046, 29 USPQ2d 2010 (Fed. Cir. 1993); In re Longi, 759 F.2d 887, 225 USPQ 645 (Fed. Cir. 1985); In re Van Ornum, 686 F.2d 937, 214 USPQ 761 (CCPA 1982); In re Vogel, 422 F.2d 438, 164 USPQ 619 (CCPA 1970); In re Thorington, 418 F.2d 528, 163 USPQ 644 (CCPA 1969).
A timely filed terminal disclaimer in compliance with 37 CFR 1.321(c) or 1.321(d) may be used to overcome an actual or provisional rejection based on nonstatutory double patenting provided the reference application or patent either is shown to be commonly owned with the examined application, or claims an invention made as a result of activities undertaken within the scope of a joint research agreement. See MPEP § 717.02 for applications subject to examination under the first inventor to file provisions of the AIA as explained in MPEP § 2159. See MPEP § 2146 et seq. for applications not subject to examination under the first inventor to file provisions of the AIA . A terminal disclaimer must be signed in compliance with 37 CFR 1.321(b).
The filing of a terminal disclaimer by itself is not a complete reply to a nonstatutory double patenting (NSDP) rejection. A complete reply requires that the terminal disclaimer be accompanied by a reply requesting reconsideration of the prior Office action. Even where the NSDP rejection is provisional the reply must be complete. See MPEP § 804, subsection I.B.1. For a reply to a non-final Office action, see 37 CFR 1.111(a). For a reply to final Office action, see 37 CFR 1.113(c). A request for reconsideration while not provided for in 37 CFR 1.113(c) may be filed after final for consideration. See MPEP §§ 706.07(e) and 714.13.
The USPTO Internet website contains terminal disclaimer forms which may be used. Please visit www.uspto.gov/patent/patents-forms. The actual filing date of the application in which the form is filed determines what form (e.g., PTO/SB/25, PTO/SB/26, PTO/AIA /25, or PTO/AIA /26) should be used. A web-based eTerminal Disclaimer may be filled out completely online using web-screens. An eTerminal Disclaimer that meets all requirements is auto-processed and approved immediately upon submission. For more information about eTerminal Disclaimers, refer to www.uspto.gov/patents/apply/applying-online/eterminal-disclaimer.
Claims 11 and 12 (both in-part) are provisionally rejected on the ground of nonstatutory double patenting as being unpatentable over claims 1-25 of copending Application No. 17/764,487 (reference application) in view of Jin et al. (cited above).
Although the claims at issue are not identical, they are not patentably distinct from each other because claim 13 includes an alkyl polyglucoside (DP 1, or a monoadduct), where R is an alkyl chain having 8 to 22 carbon atoms, and R1, R2, R3 and R4 is independently selected from
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, where R12 is
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.
It would have been obvious to substitute the structure of R12 (a citric acid derivative) with citric acid because Jin et al. teach citric acid modified alkyl polyglucosides are mild surfactants that are less irritating to eyes.
Thus, the claimed invention is prima facie obvious over the claims of the reference application in view of Jin et al.
Response to Arguments
Applicant's arguments filed 24 February 2026 have been fully considered but they are not persuasive.
Applicant contends the claims of the reference Application are drawn towards a laundry composition, while the present claims do not require all the particulars of the reference Application.
The above argument is not found persuasive, since claim 11 does not exclude a laundry composition, surfactant blend or nonionic alkyl polyglucoside crosspolymer.
Claim 11 recites the transitional phrase “comprising”, which according to MPEP 2111.03, “The transitional term "comprising", which is synonymous with "including," "containing," or "characterized by," is inclusive or open-ended and does not exclude additional, unrecited elements or method steps.”.
The structure of the functionalized alkyl polyglucoside of the reference Application is similar to that of the present claims. Its differences in the citrate moiety are taught by Jin et al.
The rejection is hereby maintained.
Conclusion
In view of the rejections to the pending claims set forth above, no claim is allowed.
THIS ACTION IS MADE FINAL. Applicant is reminded of the extension of time policy as set forth in 37 CFR 1.136(a).
A shortened statutory period for reply to this final action is set to expire THREE MONTHS from the mailing date of this action. In the event a first reply is filed within TWO MONTHS of the mailing date of this final action and the advisory action is not mailed until after the end of the THREE-MONTH shortened statutory period, then the shortened statutory period will expire on the date the advisory action is mailed, and any nonprovisional extension fee (37 CFR 1.17(a)) pursuant to 37 CFR 1.136(a) will be calculated from the mailing date of the advisory action. In no event, however, will the statutory period for reply expire later than SIX MONTHS from the mailing date of this final action.
Any inquiry concerning this communication or earlier communications from the examiner should be directed to BAHAR A CRAIGO whose telephone number is (571)270-1326. The examiner can normally be reached M-F: Noon-8pm ET.
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/BAHAR CRAIGO/
Primary Examiner
Art Unit 1699
Prosecution Insights